Caseware13d ago

Director, Professional Services

Canada·TorontoFull Time - Permanentexecutive

OtherProfessional Services

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Quick Summary

Overview

Caseware is one of Canada's original Fintech companies, having led the global audit and accounting software industry for over 30 years, with more than 500,

Technical Tools

OtherProfessional Services

Caseware is one of Canada's original Fintech companies, having led the global audit and accounting software industry for over 30 years, with more than 500,000 users across 130 countries and available in 16 different languages. While you might not have heard of us (yet) over 36,000 accounting and audit professionals list Caseware as a skill on their LinkedIn profiles!

The Director of Professional Services leads a high-performing implementation organization responsible for the successful delivery of software solutions across North America. This role owns delivery excellence, customer outcomes, and services revenue, ensuring engagements are executed efficiently, at high quality, and at scale.

The Director provides strategic and people leadership to a diverse team of project managers, consultants, trainers, and technical services professionals supporting multiple concurrent customer engagements. They are accountable for operational performance, talent development, and the continuous evolution of service offerings that drive measurable customer value and exceptional client experiences.

Working cross-functionally with Sales, Product, Product Education, and Customer Support, the Director ensures a seamless end-to-end customer journey from sale through adoption while aligning services strategy with broader business objectives. You may be required to travel to client locations and for cross functional leadership meetings when needed (up to 25%).

❗This is an existing vacancy.

❗This is a full-time, permanent position.

📍This is role is open to remote (anywhere in Canada) or hybrid (if located in Toronto, GTA), requiring the successful candidate to work three days a week at our Toronto oﬃce (351 King St E, Toronto, ON).

Ensure the successful delivery of all services engagements with a high degree of quality and customer satisfaction

Manage and grow revenue and increase value contribution through effective utilization of resources

Develop and motivate a skilled services delivery team, including conducting performance evaluations, identifying development opportunities and mentoring the team

Define and measure team performance against set objectives

Drive innovation, continuous improvement and guide the strategic direction of the team

Collaborate and work closely with the VP Professional Services and the regional professional services and education leaders to drive consistency in global processes and services for implementation and training

Actively participate in team and management meetings and strategy sessions

Foster strong customer and partner relationships to drive delivery excellence, managing feedback and escalations, as needed

Collaborate with internal stakeholders to identify and execute business growth strategies, develop hiring plans and develop supporting practices to drive product adoption

Partner with the sales and pre-sales team to complete statements of work, showcasing the value of our services team and sharing measurable outcomes

Maintain working knowledge of the Caseware solutions, industry trends and delivery methodologies

Ensure resources availability to support forecasted/planned organizational delivery expectations

10+ years’ experience in customer facing role (e.g., customer success, account management, implementation, product or project management) in a SAAS company serving the Accounting Profession OR

At least 10 years’ experience working in an Audit/Accounting/Professional Services Firm performing External Audit or Assurance engagements.

5+ years demonstrated management experience

Experience managing a diverse and remote team, including recruiting, training, staffing, and performance management

Knowledge of Caseware’s solutions is an asset

Strong operational management, project management, consulting, and process improvement skills

Experience with change management principles and resilience to adapt with pivots in strategies and goals

Demonstrated expertise supporting the sales of professional services, including developing statements of work, pricing, and large-scale proposal development including but not limited to RFI, RFQ and RFPs

Demonstrated ability to manage ambiguity and apply problem-solving skills to unique situations

Demonstrated experience succeeding in a fast-paced environment and managing multiple projects simultaneously

Excellent presentation skills, customer service, team building skills

Location & Eligibility

Where is the job

Toronto, Canada

Hybrid — some on-site time required

Who can apply

Listed under

Canada

Listing Details

Posted: April 17, 2026
First seen: April 17, 2026
Last seen: April 30, 2026

Posting Health

Days active: 13
Repost count: 0
Trust Level: 38%
Scored at: April 30, 2026

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Caseware

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Caseware International Inc. is a global leader in developing audit, assurance, financial reporting, and data analytics software for accounting firms, corporations, and governments. Founded in 1988, the Toronto-based company provides cloud-enabled solutions to over 500,000 users in 130 countries.

Employees

750

Founded

1988

Domain

Jobs

External application · ~5 min on Caseware's site

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